Every Time
by NaughtyModernFairytales
Summary: Jenny was always in control of every aspect of her life. What happens when the unexpected occurs and Nate decides he stepping in?
1. When He Calls

Sex with Nate Archibald was always painfully pleasurable.

He was so big and she was very tight. He controlled their every encounter.

That didn't stop her from going back for more, every chance she got. She craved him.

After all, pleasure and pain were just twins of one another.

When she went to him, he took. When he called her she came...and came...and came.

At the moment she was bent over his desk at the Spectator, whimpering...

"It's the middle of the day Jenny, everyone will hear you...maybe that's what you want."

Her ass was on fire from several strokes he had rendered. She couldn't help but cry out.

Her lacy little panties rested below her inflamed cheeks. He hadn't even removed them.

Nate looked down his handiwork. No one screamed like his juicy little peach. It was impossible to keep her quiet when he fucked and played with her. Her reddened ass was framed by her white lace panties. _What a picture!_ He couldn't wait...her keening told him she couldn't either. This was the first time he'd had her come to his office, and he knew some of his employees were probably getting an earful, but she was irresistible to him. She had been since the first time he was inside her.

Jenny moaned and tried to rub her throbbing clit against the desk, desperately needing fulfillment.

"Are you trying to get yourself off Peach?" He asked as he grasped her panties and ripped them from her body. "That's not allowed...a punishment is in order later."

"I just had a sp-spanking," she whimpered out as he halted her movements, and the lace rubbed against her slit as it was torn from her.

"Questioning my decisions...that's another punishment...," he said. "Open your mouth."

Trembling, she did as told. He pushed her dampened underwear between her lips and completely into her mouth. She gasped shocked, but her pussy released another gush of liquid.

Nate spread her ankles further apart, placed his cock against her opening, and thrust in to the hilt. Jenny screamed against her gag.

He began a series of slow dragging thrusts in and out of her tight channel. His shaft rubbing her swollen little pearl each time. Reaching under her, he massaged her sensitive nipples as he watched his cock disappear and withdraw.

"AH Peach! You take me so well!" He told her as he lifted her right leg onto the desk, lunging further inside.

Jenny held onto the desk and cried around her gag as Nate pounded her pussy, the way only he could. She loved how he possessed her completely leaving her no real say in the matter. She didn't think she'd ever get enough of him.

As she begin to tighten in climax, he pulled her back on his shaft hard, holding her ass against his stomach.

"Ummmmmm!" Jenny moaned as he swelled even harder within her, sending her over the edge.

Her tightness clenched him causing his cock to release a seemingly endless stream inside that soon overflowed down her silken thighs.

As he eased from her he saw his shaft covered in their combined release, and realized that this time, he'd forgotten one crucial item...the condom she asked that he always use...


	2. If It's Meant to Be

"Damn..." Nate said as he withdrew and saw his cum slip down her silken thighs. Unable to resist he caught the release with his fingers and rubbed it into her trembling pussy. He realized it was possible he was making their current dilemma worse. He simply didn't care. What happened happened. If something was meant to be, it would be.

She was beautiful in her fulfillment, lying over his desk shaking from her climax. Reaching for her mouth, he placed his dampened fingers against her bottom lip and pressed gently. She opened to him and he removed her sodden panties, quickly replacing them with his fingers. "Suck..." he told her, watching as she pulled them in, bathing them with her tongue until he slowly slid them out.

Running his hand down her back, he grabbed his boxer briefs and pants, and walked into his private bathroom and closed the door.

Jenny continued resting against his desk. When he was done with her, he would make it known. Until that time, she remained in place. This was the one area of her life where she ceded control. They had been doing this for almost a year, and over that time she had come to embrace the sexual hold he exerted.

Opening the bathroom door, Nate walked out, his clothing back in place. Carrying a damp cloth he came back to his desk and sat down. Spreading her, he cleaned the soft pink folds. Tossing the towel aside, he leaned forward and placed his tongue inside her for a brief moment, then licked her clit.

"AAH!" She cried out at his intimate kiss.

Nate backed away and pulled her dress down covering her as he lifted her from the desk. He adjusted her bra and the top of her dress. She was still trembling. "Peach it's time to go back to work."

She nodded, but still breathed a bit heavily.

"Are you aroused again from my kiss Peach?"

She just blushed, not meeting his eyes.

Nate chuckled and lifted her chin to kiss her pouty little mouth. Jenny was quickly lost, and it did nothing to cool her desire for him. Then again, that was the point.

Breaking the kiss, he looked into her eyes and said, "Yes my little peach is ripe and juicy again. A car will come for you at 8, we'll continue this evening."

Taking his jacket off the back of his chair and putting it on, he handed her the clutch she'd dropped when she arrived. Holding her hand he walked her to the door, pressing her against it, he whispered in her ear, "Can you hold out?"

Pulling away, he opened the door and offered an almost professional farewell as he left her in front of the elevator.

One Month Later...

Jenny rinsed her mouth and pressed a cold towel to her forehead. This was the fourth morning she'd woken up nauseous and running for the bathroom. At first she believed it was something she ate, but that proved to be a false theory when she gradually improved each day. She had seen illness like this before. When Blair was pregnant with Henry.

Pregnant!

But she couldn't be pregnant. They used a condom every single time, because her body was unable to tolerate most birth control methods. Using condoms was a hard and fast rule for Jenny. When they began their relationship, she had explained about birth control, and Nate agreed that he would take care of it and use condoms.

So how in the world could she be pregnant!?

Granted they were not completely effective, but she had been using them for years without mishap. Until now it would seem.

If I am, what am I gonna do!?

She wasn't worried about supporting a child. She had a job she loved and made a fantastic salary. That was the least of her problems. What would Nate think? Would he believe she was using a baby to try and trap him? What would their friends and family say? Would Nate even want to be involved? So many questions...

First things first..."Hello this is Jennifer Humphrey. I need to make an appointment with Dr. Parker as soon as possible. This afternoon at 2:45? Yes, I'll be there. Thank you."

Next she called Waldorf and let them know she would not be in. Then she decided she would return to bed for awhile until she had to get ready for her appointment. As she lay down, her cell signaled a text had arrived. Picking it up from the nightstand she saw it was from Nate.

"Where are you?! I'm in your office, but you're not here." - N

"I'm at home. I took the day off." - J

"Oh, then I'll just head over there then." - N

"NO!" - J  
Her phone rang ten seconds later. She picked up immediately.

"No? What do you mean Peach? It's been days...aren't you empty? Don't you need me to fill you...fuck you...?"

Jenny moaned at his words.

"It's ok baby...I'll be right there filling you up in a few minutes!" He said, then directed his driver to her building as he began softly telling her how he was going to have her.

"No Nate! Don't come over...I'm sick!" She called panting, having become damp and aroused from his words.

"Sick? What's wrong baby? Do you need anything? I'm just going to come and check for myself."

"No you don't have to...Really! I'm fine. I even have a doctor's appointment this afternoon to make sure. You just go on to work, and I'll call you this evening. I was about to go back to sleep anyway."

"If you're sure you're okay? What time is your appointment? Do you want me to go with you?"

"NO! I mean, no I'm fine. It's just a routine check up. Well let me get back to sleep before it's time to go. Bye Nate." She said yawning for effect as she disconnected the call.

Jenny placed the phone back on her nightstand, then pulled the covers around her. She was asleep almost as soon as her head hit the pillow.

Nate knew Jenny was hiding something. Sure she was fiercely independent and their involvement was suppose to be secret, but he wanted her to come to him if she needed anything. He had loved Jenny Humphrey for so long. When she moved away to Hudson, then Paris, he didn't think he'd ever have the chance to truly be with her. Then she came home for Dan and Serena's wedding and to launch her new label.

He was drawn to her just as he had always been. After several tries, he finally got her to agree to have coffee with him. Over the course of a few weeks, they met many times, the conversation flowing smoothly as ever between them. He had missed his friend.

At the end of January The Spectator hosted a gala for new investors. He wanted her to be his date, but she declined. However she did agree to attend. He had trouble taking his eyes off her all night. She'd always been stunning in black, and that night was no exception. She wore a strapless black brocade sheath shot through with gold threads and slit to the middle of her left thigh. Thank goodness his tuxedo jacket covered his constant hard-on.

He offered her a ride home that evening. To his home, as it turned out. He couldn't resist touching her in the back of the limo. As they kissed, he slid his hand between her thighs, finding her panties soaked.

"You're wet Jen..."

"You always make wet Nate..."

"Lets see if I can make you come..." He said, thrusting three fingers into her. She screamed as she orgasmed and he kissed her taking it in.

At his penthouse, he finally got to have her, as he'd wanted to for so long. He barely lasted three minutes the first time with her pressed against the foyer wall as he drove into her tightness. For the next 12 hours he fucked her in a myriad of positions on any given surface of his apartment. He thought this would slake his long time desire for her, but it only increased. She took him into her over and over, reveling in every climax. He knew he didn't want what had begun to end, he wanted it to become more.

However, Jenny didn't see it exactly the same way. She had enjoyed the sex, but said that was all it was or could ever be. She was willing to have a monogamous sexual relationship with him, if he would agree to her terms. She requested their relationship be a complete secret and that he use condoms each time, just as they had during the last several hours. She was unable to take birth control internally, so condoms were the best option.

Nate was heartbroken that she couldn't see more between them. He wanted to tell her that he had feelings for her, but she was so resistant. The last thing he wanted to do was drive her away. So he agreed, but with stipulations of his own. Whenever or wherever he called for her, she must come to him and let him have her. Surprisingly she agreed. He later learned that she liked someone else being in control of some part of her life. As far as he was concerned he would be the only one who would ever control this aspect.

His thoughts returned to the present as he tried to figure out what could be going on with her. Pulling up in front of her building, he got out of the car and walked over to the doorman.

"Good Morning Steven!"

"Good Morning Mr. Archibald! Ms Humphrey hasn't come down yet."

"Oh she's not feeling well today, so she won't be going to work."

"I'm sorry to hear that. I hope she feels better soon."

"Thanks, I'll pass that along. Steven, I was wondering if you could do me a small favor?"

"Yes Mr. Archibald?"

"Ms. Humphrey has a doctor's appointment this afternoon, and I'd appreciate it if you would call me when she rings down for a cab. Then I'll know what time her appointment is."

"I don't know Mr. Archibald...can't you just go up and ask her?"

"Oh she's resting. I don't want to wake her. You understand."

"Oh ok. In that case, sure I'll call you once she rings down."

"Thanks! Here, take your wife someplace special." Nate said, slipping the doorman a hundred.

"Thank you Mr. Archibald! I'll call you."

Nate waved and got back in his car, directing his driver to The Spectator.


	3. Consequences

Chapter 3

"Mr. Archibald, it's Steven. Ms. Humphrey just called down for a taxi."

Nate looked at his watch. It was 2PM.

"Thanks Steven."

"No problem. Bye Mr. Archibald."

Nate told his assistant he was leaving for the day and took the elevator down to the lobby. He exited and went to get in his town car which waited at the curb. As he settled in, his driver returned to Jenny's building and parked a discreet distance from the entrance. At 2:20, she came out of the building and got into the waiting taxi. It pulled away from the curb and his driver followed at a distance. Within ten minutes the taxi pulled up at the Midtown Medical Complex. Jenny entered the building and signed in at the security desk. Nate followed at a safe distance. Entering the building he walked over to sign in. Luck was with him, visitors had to write which floor they were going to and the suite number, and she was headed to 404.

In the elevator he hit the button for the fourth floor. On four he walked casually to the suite. Looking through the glass he saw Jenny was already being taken in back. Dammit! He had no idea what her doctor's name was. Hopefully his level of charm was still high he thought as he pushed open the door. Approaching the counter he heard one of the two women there answer a call, "Women's Health Consulting...may I help you?"

Nate's steps slowed as he heard "Women's" being spoken. Glancing back at the door, he noticed that name was etched on the door along with the names of Doctors Aaron Parker, Rachel Fine, and Daniel Bauer. All of whom were also listed as obstetricians and gynecologists!

He stood there stunned. Was his Peach pregnant?

***

Jenny sat nervously in the examination room. They had taken samples to find out if she was pregnant. Dr. Parker would be in momentarily with the results.

She tried to remain calm, but she was so close to losing it. If she was pregnant, and she was certain she was even without the results, she had no idea what she was going to do! Waiting like this was a slow torture...

Nate hadn't moved in five minutes. He sat just inside the waiting area. Was his child now growing inside Jenny? He had so many questions. And even with all the unknown, he was ecstatic!

If Jenny was pregnant maybe he could get her to see that what's between then could be so much more. When he had forgotten the condom that day, his mind and heart were in complete agreement that he would not only accept, but welcome the consequences of that action. He hadn't even told her that he'd made love to her without protection. Maybe a part of him wanted a way to bind her to him...if so, this was most certainly it.

One of the assistants at the counter noticed him sitting there sans girlfriend or wife, and called out, "May I help you sir?"

Looking up at her, Nate flashed her a winning smile as he tried to come up with a plan to get him back there to Jenny.

"Hello, I'm Nate Archibald." He said walking up to the counter.

"Good Afternoon Mr. Archibald. Are you waiting for someone?"

"No-I mean yes...my girlfr- um, fiancé is in the back, and I wanted to go back and be with her."

"If you can just tell me her name and which doctor she's here to see I can call back and-"

"No that won't work!" He said cutting her off.

"Excuse me?"

"I want to surprise her. She's not expecting me."

"I'm sorry sir. I can't just send you back there. You're welcome to continue waiting here."

"Please! She's about to find out if we're going to have a baby! I need to be there!"

She looked at him for a moment. "What's her name?"

"Jenny Humphrey."

"Just a moment," said as she called for someone in the back, "Marin!"

Another woman appeared and she asked her something he couldn't hear.

"Alright Mr. Archibald, Marin will take you back. I just hope we don't get fired for this..."

"Thank You! Here's my card, if you have any problems, give me a call."

She looked at the card and nodded, as he turned and followed the woman she had called Marin.

"Ok sir, Ms. Humphrey is in there waiting for the doctor, who will be in shortly."

"Thank you."

Nate turned knob and eased the door open. Jenny sat on the end of an examination table, her face in her hands. She hadn't heard him come in. Jennifer Humphrey is a ball buster, an ass kicker. This woman looked as if she had the world on her shoulders and it was taking her down. He closed the door behind him softly and went to stand in front of her. She looked up and saw him, her tear filled eyes widening.

"What the hell are you doing here Nate!?"

"I could ask you a similar question."

"I told you I was going to the doctor." She said nervously.

"Yes you did, but you failed to mention what kind of doctor..."

"I-I-I..."

"No response to that? It's okay. I'll just ask one question...are you pregnant Peach?" He asked against her temple. His hands rested on either side of her hips, boxing her in.

She looked at him tears streaming from her eyes. "I don't know. The doctor..."

"Oh the doctor hasn't confirmed it yet. You're pretty sure you are though, aren't you?"

"Y-Yes."

"What were you gonna do Peach? Run? Hide? Keep me in the dark?"

"I don't know...I just realized I was...wanted confirmation..."

"Well Great! We can both be here for the good news, then you and I have a lot to discuss."

"I'm not ready to..."

"But I am! From here on out I'm in control..." He said holding her trembling body tightly against his chest.

Oh God! How did this happen!? She thought as the doctor walked in.


	4. Needs

Three months later...

Jenny lay sprawled over Nate's chest, her right ear pressed against his fast beating heart. She moaned as he held her hips, moving her on his cock. This is how her day had begun for the past week. In spite of everything that had happened over the last few months, _this _hadn't changed. They still shared an overwhelming desire for one another.

_She was the one who had awakened the beast, so to speak. At four months pregnant, Jenny was in a phase. She was horny as hell! A few mornings ago, she had woken up with her nipples hard and her pussy craving Nate. Unable to resist, she'd slid between his legs, released him from his boxers, and taken him into her mouth. He had hardened and expanded as she worked him with her tongue and gently squeezed his balls. She ran her other hand between her thighs, massaging her clit. Jenny had taken him deeper, easing him just into her throat, her nose pressed against him. His musky scent aroused her even more, and she moaned around his hardness. _

_Nate had awoken as she grasped his balls. He watched her with heavy lidded eyes, and threaded his fingers in her hair, pulling her on to him, "That's right baby...take me in...," he murmured as their eyes met. Neither looked away as she took him deep, then pulled back sucking his cock head gently. _

"_Come here Peach...shift around...I need my mouth on you..." _

_Jenny sat up on her knees looking a little dazed, her hand still working between her thighs. _

"_No, that's a naughty Peach!" he said, pulling her hand away from her body. _

"_Nate...Please...I need..." she practically begged._

"_I know what you need baby. Come up here..." he said, holding her hand as she moved to kneel by his head resting on a pillow. Placing his hand against her, he dragged his finger through her folds._

"_Umm..." she moaned._

"_I know Peach...come on...kneel over me baby. I'm gonna give you what you need." he said, cupping her right hip._

_Trembling, Jenny kneeled over his head, her center right above his mouth. He blew a light breath against her and she shuddered. Then he simply dove in, his tongue tunneling into her. She couldn't help grinding against his mouth. The shudders increased throwing her over the edge, crying out as she fell forward against his hip. As she slowly returned to earth, she noticed two things. Nate's tongue lapped at her clit as his fingers thrust inside her, and his cock throbbed mere inches from where she rested, a pearl drop on the tip. Leaning over, she took him back in, sucking him in small strokes._

_Feeling her hot little mouth around him once again, Nate thrust his fingers into her, rubbing the meshy front of her pussy and biting down as he sucked on her swollen clit._

_Jenny screamed as another climax rolled through her and a small stream of release pulsed from him. Both accepted what the other gave. She continued stroking his hard shaft as his intimate kiss became long, slow laps of his tongue. _

_Lying there, replete from her orgasms, Jenny whimpered softly as Nate lifted her from his mouth and eased her down his torso. Behind her, he whispered, "Rise up baby." Limp as a rag doll, she knelt over him. He placed his cock at her opening, and she took him in. "That's my Peach...so tight!" She sat there with him inside her and absorbed the feeling. He ran his hands over her, rubbing her soft skin. She trembled and moaned. Her legs were still shaky from coming, preventing her usual all out ride. Multiple orgasms and pregnancy apparently made for a tired Jenny. _

_Nate felt her trembling. Sitting up, he placed his mouth against her ear. "Too tired to finish what you started baby?"_

"_Nate! Please!"_

_Pulling her mouth to the side, he took it in a deep kiss. Placing another pillow behind him, he lay back taking her with. Their kiss continued as he teased and tormented her breasts. Her nipples tightened and she whimpered. Jenny reclined against him, his hardness inside her, legs spread on either side of his. Nate lifted his knees and held her waist as he began thrusting into her. Rolling her hips, she met each thrust. Several minutes later, he grasped her hips, holding her as he fucked into her deep and hard. Jenny cried out as her climax overtook her. His release followed as her channel contracted around him. _

_Nate slid from her and held her to his side. He kissed her forehead her rubbed her back. _

The next morning he initiated their interlude, then she did so again the following day. They alternated like that all week. On the days she got them started, Nate inevitably guided their path to the finish. This morning he'd kissed and stroked her awake. Not drawing the lovemaking out this day, he'd pulled her astride him after a few minutes and plunged in. She listened to his heart pound, as he stroked her up and down. Jenny circled her hips and her clit brushed against him. Grinding against him in rhythm, she reached between them and massaged his balls. Nate came as her hand and pussy gripped him. Holding her against him, he ground the base of his dick against her clit, making her scream through her orgasm.

"Peach, you really know how to satisfy your husband."


End file.
